Dan’s group of buddies needed one final participant for their Fantasy Football Draft, and Riley was in the right place at the right time (Vanderslice Hall). She eagerly offered to join, but she didn't have her laptop with her. Dan, who had only just met Riley, offered to let her share his computer. Riley was struck by his chivalry, and Dan was struck by her boldness. They became best friends, and from there it was only a matter of weeks before they fell for each other!
Dan planned a relaxing weekend away at Mohonk Mountain House. On Saturday, despite his nerves, Dan ordered lobster bisque and chicken and waffles for lunch, keeping any of Riley's suspicions of a proposal at bay. However, later that day at the top of the windy Sky Top Tower, Dan asked Riley to marry him overlooking New York, Massachusetts, Connecticut, New Jersey, and Vermont - all states with significance to the couple. Riley yelled "of course!"